Controlled Photochemical Synthesis of Substituted Isoquinoline-1,3,4(2H)-triones, 3-Hydroxyisoindolin-1-ones, and Phthalimides via Amidyl Radical Cyclization Cascade
2022
Reddy, Mandapati Bhargava | Prasanth, Kesavan | Anandhan, Ramasamy
We report a controlled radical cyclization cascade of isoquinoline-1,3,4(2H)-triones, 3-hydroxyisoindolin-1-ones, and phthalimides from o-alkynylated benzamides by metal-free photoredox catalyzed amidyl N-centered radical addition to the C–C triple bond using the proton-coupled electron transfer (PCET) process under mild reaction conditions. A time tunable synthesis of 3-hydroxyisoindolin-1-ones and phthalimides via β-carbonyl-C(sp³) bond cleavage was also achieved under visible light irradiation. A mechanistic rationale for the radical cyclization cascade is supported by various control and quenching experiments as well as EPR studies.
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